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1-(2,6,6-Trimethylcyclohex-3-en-1-yl)but-2-en-1-one → Methyl 2-(4-oxo-4-(2,6,6-trimethylcyclohex-3-enyl)butan-2-ylamino)-3-(4-oxo-4-(2,6,6-trimethylcyclohex-3-enyl)butan-2-ylthio)propanoate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1-(2,6,6-Trimethylcyclohex-3-en-1-yl)but-2-en-1-one | HCID 42296 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | L-Cysteine, methyl ester, hydrochloride | HCID 2733208 | — |
| 溶媒 | Methanol | HCID 887 | — |
| 生成物 | Methyl 2-(4-oxo-4-(2,6,6-trimethylcyclohex-3-enyl)butan-2-ylamino)-3-(4-oxo-4-(2,6,6-trimethylcyclohex-3-enyl)butan-2-ylthio)propanoate | HCID 68635878 | 82% |
反応手順
A solution of 1-(2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one (19.28 g, 100 mmol, 2 equiv.), ethyl diisopropylamine (6.45 g, 50 mmol, 1 equiv.) and L-Cystein methyl ester hydrochloride (8.60 g, 50 mmol, 1 equiv.) in MeOH (120 ml) is heated to reflux during 28 h. The solvent is removed in vacuo and the residue dissolved in methyl t-butyl ether. The solution is washed with dilute aq. NaCl, dried over MgSO4 and concentrated. The residue is purified by chromatography on SiO2 to yield 21.3 g (82%) of the title compound as yellowish, viscous oil.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07846887B2 |
| 出典データセット | uspto-grants-2010_12 |
| ORD ID | ord-c9b7ced433ec4f2986752cd133d4161c |
| 出典メモ | uspto-grants-2010_12 |